Issue 43, 2010

Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition–elimination reaction

Abstract

A catalytic domino reaction producing substituted 2-alkylidenecyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis–Hillman adducts, and α,β-unsaturated ketones is described. The process involves two mechanistically distinct reactions, (4+2) cycloaddition and elimination. Both of these reactions are catalyzed by Tf2NH.

Graphical abstract: Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition–elimination reaction

Supplementary files

Article information

Article type
Communication
Submitted
18 Aug 2010
Accepted
14 Sep 2010
First published
28 Sep 2010

Chem. Commun., 2010,46, 8246-8248

Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloadditionelimination reaction

K. Takasu, T. Tanaka, T. Azuma and Y. Takemoto, Chem. Commun., 2010, 46, 8246 DOI: 10.1039/C0CC03336G

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